Trisazo dyestuffs



.- 2,718,518 Patented Sept. 20, 1955 1 2 2,718,518 Example 1 TRISAZO DYESTUFFS 201 parts of 1-amino-2,4-dimethylbenzene-G-sulfonic Fritz suckfiiu, Level'kusen'wiesdom and Paul zervas, acid are diazotized with 69 parts of sodium nitrite in f i i g s fi a g s hydrochloric acid solution at 5 C. 137 parts of 1- en ayer engese ver sen, ermany 5 amino-Z-methoxy-S-methylbenzene are added to the diazo acorporation of Germany compound and con I plmg is being fimshed by adding No .g is zgiag 1952 sodium acetate. The isolated monoazo dyestulf is disan A r 3 1951 solved in caustic soda solution and after adding 69 parts Calms PHOHtYaPPHcafiW Germany P 2 of sodium nitrite indirectly diazotized at 5 to 8 C. 5 Chums- 260-173) 10 The diazo compound thus obtained is coupled in sodium The present invention relates to new trisazo dyestuffs carbonate alkaline medium with 358 parts of 2-(4'-aminoand to a method of making the same; more particularly benzoylamino)-5-hydroxynaphthalene-7-sulfonic acid at it relates to trisazo dyestuffs corresponding to the general 0 C.; the disazo dyestutf is isolated. It is slurried up and formula: if further diazotized with 69 parts of sodium nitrite for Hols r111, non NELCOON=N AN=NBN= H H In this formula A-N=N-B stands for the radical of 1 /2 hours at 20 C.; the final coupling is performed in a diazotized aminomonoazo dyestulf containing at least sodium carbonate alkaline medium with 319 parts of 2- one sulf nic a id grou amino-5-hydroxynaphthalene-1,7-disulfonic acid at 0 C.

The new trisazo dyestufis can be obtained by coupling After being isolated and dried, the trisazo dyestuif reprea diazotized aminomonoazo dyestuif containing at least sents a dark powder which easily dissolves in water with one water-solubilizing group such as the sulfonic or the a violet color. When dyed on cotton and developed with carboxylic acid group and wherein A and B of the above 2-hydroxynaphthalene, a very clear violet is obtained.

formula may belong to benzene or naphthalene series, In the form of the free acid the dyestuff corresponds with 2-(4'-aminobenzoylamino)-5-hydroxynaphthalene-7- to the formula:

sulfonic acid, further diazotizing the aminodisazo dye- H033 NH: 8101B on, Hots NH.o0O-N=N H: OH: H

stuff thus obtained and coupling it with Z-amino-S-hy- Example 2 dfoxynaphihalfme-1,7-d1$lllf011i acid- When replacing in Example 1 the l-amino-Z-methoxy- The new tnsazo dyestuffs yield on cotton and fibres s h lb b 121 parts of 1- i -2,5-dj th 1.

of regenerated cellulose red to blue-violet dyemgs which b a d stuif i b i d which, after developing can be diazotized on the fibre and developed with 2-hywith Z-hydroxynaphthalene, dyes cotton very clear ruby droxynaphthalene to bluish red to reddish blue shades. shades.

final component Z-amino-S-hydroxynaphthalene-7-sul- Example 3 fonic acid instead of Z-amino-S-hydroxynaphthalene-1,7- wh replacing i Example 1 h Laminmlmethoxy.

disulfonic acid in essentially clearer shades of the Sqnethylbenzene by 1 parts of l-amino-z,s-dimethoxydyelngs developed with z'hydloxynaphthalenebenzene, a dystutf is obtained which, after developing The following examples illustrate the Present invention with Z-hydroxynaphthalene, dyes cotton clear blue-violet without, however, limiting it thereto, the parts being by 65 shades.

i h The dyestufi corresponds as free acid to the formula:

The new dyestulfs excel known dyestuffs containing as As free acid the dyestuff corresponds to the formula:

HO|S -NH: son; on. 110.5 NH.COON=N omQN= QN=N H H; n, H l

3 Example 4 V i We claim: l. Trisazo dyestuffs Corresponding as free acids to the 123 parts of 1-aminobenze'ne-3-sulfonic acid are diazogeneral fo la:

tizedwith 69 parts of sodium nitrite and coupled with 107 wherein A is an aromatic 'rnonosuifuric acid radical of parts of 1-amino-3-methylbenzene. After further diazothe benzene series, and B is. an aromatic radical of the tizingat 20 C. it is coupled with 358 parts of 2-(4-amino- 15 benzene series free from sulfonicacid radicals. benzoylamino)v-5.-hydroxynaphthalene-7-sulfonic acid in 2. The trisazo dyestuff corresponding as free acid to the the presence ofsodium bicarbonate and the disazo dyeformula:

SOaH

' HO3S NHz SIO3H CH3 7 1103s NH.oo--N=N- H.O@ N=N@ N=N H CH3 OCHs 6H stufi is isolated. Further diazotizing is performed with 69 i 3. The trisazo dyestufi corresponding as free acid to parts of sodium nitrite at 20 C., and final coupling is the formula:

' SIOSH HOsS- NH:

s 0311 $113 HOaS- -NH.O o N=N E30 N=N N=N OH 0H3 in OH carried through with 319 parts of Z-arnino-S-hydroxy- 4. The trisazo dyestuff corresponding as free acid to naphthalene-1,7-disulfonic acid in sodium carbonate althe formula:

S|O3H SOaH 0cm ms kaline medium. After being isolated and dried, the dye- 5. The trisazo dyestufi corresponding as free acid to stuff represents a dark powder. When dyed on cotton the formula:

SOaH

H033 NH,

i HOaS NH.CO

' OsH Ha H and developed with Z-hydroxynaphthalene, a very clear References Cited in the file of this Patent Bordeaux iS obtained. UNITED STATES PATENTS The new dye'stuff corresponds in the form of the free 65 1,716,098 Woodward June 4 1929 331d to the form la: 2,351,118 HaddoCk sue- June 13, 1944 SOaH 

1. TRISAZO DYESTUFFS CORRESPONDING AS FREE ACIDS TO THE GENERAL FORMULA: 